The Five Saddest Songs Ever Written


Feeling down and want that extra push into suicide land?

Here are your five best bets:

(5) “Hello, It’s Me,” by Todd Rundgren

The simple, conversational tone, along with dark feelings like, “Maybe I think too much, but something’s wrong,” make this 1968 classic achingly intimate. Its raw sweetness slays me every time.

(4) “Anyone Who Had a Heart,” by Burt Bacharach/Hal David

A wail of a bad time and a mashochist’s wet dream, this 1963 chart topper is also a great venue for a vocalist wanting to play victim and belt out some hurt. Number one with a hankie.

(3) “If Love Were All,” by Noël Coward

The dark side of Britain’s longtime court jester, this deceptively simple ballad is a plainly stated, deeply felt, and very wise plaint for true romance.

“I believe the more you love a man / The more you give your trust / The more you’re bound to lose.” Been there!

(2) “Smile,” by Charlie Chaplin, John Turner, and Geoffrey Parsons

Intended as a cheer-up song to someone whose heart is loudly breaking, this classic always ends up making everyone feel worse. The melody is so sweet and brittle and the emotions so raw that the singer usually starts falling apart while singing, “Light up your face with gladness / Hide every trace of sadness …” Killer shit.

And the winner…

(1) “Good Morning Heartache,” sung by Billie Holiday

The ultimate depressed person’s cry of submission, “Heartache” welcomed a mood spiral at a time before the right meds were on the market. Lines like, “You old gloomy sight / Thought we said goodbye last night,” are bone-chilling in their resignation. By time Billie tells heartbreak to just “sit down,” the razor’s on the wrist, and I’m sort of loving it.